After a recent penetration test report-out call with a client, I asked my interns if anything from the call surprised them. One of them noted that he was surprised how “chill” the call was. That was interesting to me because it reminded me that I had thought the exact same thing when I first got into consulting and pentesting. It’s easy to see how a readout call could be an incredibly tense, combative affair but in my experience the best pentesters manage to not only avoid that but reverse it.

The mood of the report-out call is an excellent barometer for something that’s critical, and often lacking, in our industry: a constructive relationship between the red team and blue team. While critical, it’s also subtle, and creating the conditions for a good relationship is a process that requires real work and empathy for everyone at the table. My advice: Start Early, Be Meticulously Professional, and Remember the Goal.

Start Early

If the goal is a relaxed, productive, (even “fun”) readout call, then the groundwork must start early. While there are other things that come before it, a detailed kickoff is really the first big chance to get moving in the right direction. As a tester your goal should be to make sure that everyone is clear and comfortable with what’s about to happen, and what exactly the client hopes to get out of it. The behavior ends up being a combination of a lot of standard questions, and sniffing around for any hint that there are either concerns or complexities going unaddressed. It’s also important at this point to really understand context from the client’s view. What’s a critical vs. a high or medium? What do they care less about than you might expect them to? Why? The more understanding you have now, the more that the entire report can be placed in context. If it feels like you’re facilitating a group therapy session where the clients are sharing their (security-relevant) hopes and their fears, then you’re probably doing something right. My team literally asks questions like “what keeps you up at night?” and “what’s the scariest thing we could do here?” Asking the big questions frankly and early helps take the elephant out of the room and moves toward productive discussion of the big questions rather than tentatively working up to them through peripheral issues.

Aside from the kickoff meeting itself, “start early” means start doing things well now so that you have a buffer of goodwill to draw on later. I’ve heard it called an “emotional bank account”: make people feel good about you, make a deposit; let them down, make a withdrawal. Ideally you always want that balance going up, but when something happens (and it’s definitely going to), you want to make sure that you’ve got a nice buffer of goodwill so that it’s understood that it was a blip in an otherwise solid relationship. Neil Gaiman once explained that people keep working because their work is good, they’re pleasant to work with, and because they deliver on time. But the secret, he says, is that it only takes two out of the three. Different people are going to be able to take a different two for granted, but know that if you always shoot for all three you’ve bought yourself some leeway if something happens.

Be Meticulously Professional

Beyond simply good will, one of the important reasons clients call in pentesters (or consultants of any kind) is to get that feeling that they’re in good hands; that someone is going to make sure that messy, complex things get taken care of properly. We’re expected to drop into situations where deadlines, resources, or nerves are already in trouble and provide some useful answers and confidence that the “Right Things” are being done. So, standard consulting practices like “Communicate well and often”, and “Don’t surprise people” apply, of course.

But one area that security folks sometimes struggle with is ego. There typically are already plenty of personalities and internal politics involved; that makes it critical for us as outsiders to not bring further ego into the situation.

This ego can take a few forms. The first is a tendency toward fearmongering and overselling findings; wanting to be perceived as one of those “scary hacker types”. That can be helpful (to a point) for establishing technical credibility but it’s important to realize that being cool isn’t in the job description. Likewise, neither is taking credit or passing blame. Remember: Amateurs get credit, professionals get paid. The rule for blame is similar: as in the airport in Fight Club, never imply ownership of the bug. If the goal is to make something more secure, it’s rarely relevant who exactly created a bug when it’s likely process, tooling, or training that really needs to change.

I hear security absolutism in language like “Windows sucks because…” or “Well, actually there’s no point in fixing that because hackers could still…” (or really anytime someone starts handwaving about esoteric TLS attacks or Van Eck phreaking … you know the type).

Real professionals need to be able to set aside the hacker mindset long enough to have productive, nuanced discussions about how to fix things. There are rarely perfect solutions, and the imperfect ones come with tradeoffs. We should all be willing to be as pragmatic on defense as we are on offense. The perception that security people are going to naysay or ridicule every suggestion hurts all of us, and makes us less effective as an industry. The “Nick Burns” mentality is a self-reinforcing stereotype we need to fight against at each encounter. Similarly, there’s an odor of superiority that often comes off some pentesters when they break a thing and speak about it publicly, as if that somehow demonstrates that they are smarter than the person who designed it. Sometimes a thing is *so* bad that an example must be made, but for my tastes those instances are far more rare than twitter and blogs would make you think.

Even if a client is a pain to work with, doesn’t take good advice, and fights you on everything, they made at least one smart call: they asked for help. The better we’re able to appreciate that, understand their perspective, and work toward improving the system, the better the relationship and better the results. I’ll feel happier about our industry when dev and ops actually look forward to their calls with security folks, and I’ll tell you this: life’s a lot better when we look forward to them too. So remember; be professional, be empathetic, be helpful — and be chill.

One Response to “On Pentesting, Professionalism, & “Chill””

This is terrific and insightful stuff. I’m very proud to count you among my friends and to see myself in an industry where we can surround each other with good thoughts and good advice like yours.

I totally realize that in the past I have asked my own version of the “What keeps you up at night” question without realizing it. Seeing you put it into words so plainly guarantees me that I will explicitly ask some variety of that every single time from now on.

Ironically, I think a handful of times I have asked the question it has been after the assessment. Almost inevitably, the answer at that point simply comes back: “you.” 🙂